Winchester Vacation Packages

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Your Winchester Vacation

History, cuisine, art and more … There's so much to discover with a Winchester vacation package. And with the ability to customize your city break, it's guaranteed to be one you won't forget. Eager to start exploring your surroundings? Fair Hill State Natural Resources Management Area, Patriots Glen Golf Club and East Meadow Park are among the leading places to visit during your trip to Winchester. Your dream Winchester vacation is a couple of clicks away. Search accommodations, flights and more on Expedia for an adventure that's tailored to suit your style.

Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Price was CA $829, price is now CA $598 per person
CA $598
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
8.2/10 Very Good! (1,006 reviews)
Convenient external room door made it easy walking my dog. Did not have to walk thru.obby.

Reviewed on Aug. 24, 2025

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

4 out of 5
Inner Harbor
Price was CA $1,188, price is now CA $881 per person
CA $881
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
8.6/10 Excellent! (2,299 reviews)
Clean, friendly staff, great area

Reviewed on Aug. 24, 2025

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was CA $1,264, price is now CA $942 per person
CA $942
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
Expected more from a sheraton

Reviewed on Aug. 25, 2025

Hotel Indigo Baltimore Downtown by IHG

Hotel Indigo Baltimore Downtown by IHG

4 out of 5
Mount Vernon
Price was CA $1,107, price is now CA $825 per person
CA $825
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
9.2/10 Wonderful! (1,000 reviews)
Beautiful hotel with attentive staff. Not in a walkable part of town, but we took Ubers.. Hotel bar was very nice!!

Reviewed on Aug. 25, 2025

Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Inner Harbor
Price was CA $949, price is now CA $714 per person
CA $714
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
8.2/10 Very Good! (680 reviews)
Dated but very hospitable

Reviewed on Aug. 25, 2025

Ready to book your vacation to Winchester?

 

Choose your dates

Winchester Hotel Deals

Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

3 out of 5
48 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Aug 28 to Aug 29
CA $134
CA $148 total
Aug 28 - Aug 29
includes taxes & fees
7.8/10 Good! (1,082 reviews)
"I’ve stayed here multiple times in this last time was probably the best. The staff was very helpful and courteous, and the amenities were top-notch."

Reviewed on Aug. 18, 2025

Sonesta Select Newark Christiana Mall
DoubleTree by Hilton Downtown Wilmington - Legal District

DoubleTree by Hilton Downtown Wilmington - Legal District

4 out of 5
700 N King St, Wilmington, DE
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Sep 2 to Sep 3
CA $125
CA $137 total
Sep 2 - Sep 3
includes taxes & fees
7.2/10 Good! (1,006 reviews)
"It was an easy checkin experience and the room is good for just a 1-3 night stay. Shower water was nice and hot."

Reviewed on Aug. 22, 2025

DoubleTree by Hilton Downtown Wilmington - Legal District
Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Sep 9 to Sep 10
CA $87
CA $97 total
Sep 9 - Sep 10
includes taxes & fees
5/10 (1,002 reviews)
"There is a door that is tetanus waiting to happen its rusy and my friend cut her hand trying to get to the second floor. But the staff is amazing . The man who checked us in was great. The room was clean however they should get new beds in 242 they are loud and a little uncomfy but for a night or ..."

Reviewed on Aug. 21, 2025

Quality Inn Newark - Wilmington
See all 614 properties in Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Discover the most popular places to visit in Winchester

Elkton Indoor Tennis

You can take time to visit Elkton Indoor Tennis during your travels to Elkton. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Elkton Indoor Tennis

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from CA $598 on Expedia for your Winchester break. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
If you're hoping to score a cheap Winchester vacation package, consider visiting in January, February and November. You'll generally find lower prices on flights and accommodations during these months — perfect for a budget-friendly getaway.
How many days is enough for Winchester?
The ideal length of your Winchester vacation depends on what you'd like to see. Typically, a few days to a week will give you enough time to visit all the leading sights and explore some hidden spots along the way.
How to find the best Winchester package deals?
Finding a cheap Winchester package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Winchester package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Winchester vacation as a package?
You can enjoy significant savings on your Winchester getaway by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winchester?
If you've got your Winchester travel dates locked in, book early to snap up some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Winchester?

  1. Choose when to travel: Check your calendar and get packing. Your favourite season and the type of activities available will also help you decide when to escape to Winchester.
  2. Plan your budget wisely: On top of the cost of your hotel, you'll need to factor in other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that could crop up during your trip to Winchester.
  3. Set the duration of your trip: Start by listing all the attractions you'd like to get to in Winchester. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Winchester vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.